Estate taxes generally can be minimized – though, for wealthy families, they are rarely eliminated altogether.¹ With careful planning, you can reduce the amount your estate ultimately owes and ensure the taxes will be paid as efficiently as possible.

Such planning is especially important when an estate has illiquid assets, such as closely held business interests, real estate or art. Without a plan, estates too often lack sufficient cash to pay the tax bill when it comes due.

How will you prepare your estate to preserve wealth and protect your family’s future? Here, we offer a quick look at five strategies so you can consider which might work best for you and your loved ones.

Simplest is to use cash or liquid assets

Usually, executors have only nine months from date of death to pay U.S. estate taxes.² Thus, using cash or selling liquid assets might seem like an easy and logical choice. In fact, most executors take this approach, though only sometimes is it for sound financial reasons. More often, it is the result of an executor attempting to tidy a mess left behind by the decedent; to preserve family harmony; or simply to move matters forward unaware that alternatives are available.

However, it may not be in the best interests of the beneficiaries to deplete a significant portion of an estate’s liquidity.

Still, the upside of this option is that there are no financing costs. Also, selling assets can usually be done in a tax-efficient manner, as beneficiaries would likely inherit those assets (especially any marketable securities) with a basis adjusted (usually up) to their fair market value as of the date of death.

Using available liquidity is more likely to net the estate full value than selling illiquid assets in a forced sale – especially if those illiquid assets include a closely held business in which the beneficiaries will continue to be involved. Note, though, that U.S. tax law offers relief (in the form of what can be a lengthy extension of time – even up to 15 years) to the estates of closely held business owners, recognizing that a quick, forced sale of assets is unlikely to deliver full value to the estate’s beneficiaries.

Buy peace of mind with life insurance

Owning life insurance now (either directly or through a tax-efficient trust) can be an effective way to pay estate taxes later. We see more and more clients acquire insurance for this purpose.

Two basic types of policies can be used for estate tax purposes:

• Term insurance – which provides a level premium and death benefit for a stated period of time
• Permanent insurance – which requires a higher initial premium and accumulates a cash value over time

For example, you might buy a life insurance policy in anticipation that your executor would use the proceeds to pay estate taxes due. This technique can be particularly useful for families with illiquid assets that would not provide sufficient liquidity for projected estate taxes (or other expenses).

To help pay estate taxes, married couples will sometimes buy “second-to-die” (survivorship) life insurance, since the unlimited marital deduction, often eliminates the estate taxes on the death of the first spouse to die. In such cases, taxes are not due until the surviving spouse passes away.

Owners of a closely held business might also consider a life insurance policy to backstop buy-sell provisions in the company’s operating agreement that are triggered when one of the owners passes away.

Insurance is commonly held in an entity outside of the decedent’s estate, for example, in an irrevocable life insurance trust (ILIT).

Borrow to avoid a forced sale

Borrowing to pay estate taxes can prevent the forced sale of closely held business interests, preserve valuation discounts (typically, “lack of marketability” and “minority interest” discounts) and free up liquidity. But be sure to consider how the estate will pay the interest and principal on the amount borrowed. Ideally, investment income generated by the assets retained, or surplus cash flow from an operating business, can be used to pay those costs.

Also consider how borrowing will affect the beneficiaries’ future needs and outlook for the business (e.g., market environment, liquidity requirements).

We find many clients with largely illiquid estates do not think through the heavy cash needs their executors will have to face. While this happens for a variety of reasons, the consequence is that those executors are forced, on a tight timetable, to choose among often unattractive options.

Here are two financing options to consider:

Borrow from the IRS

U.S. tax law offers some relief to estates that include a closely held business (including certain farm assets) that has a value exceeding 35% of a decedent’s estate.

Qualifying estates may defer part, or even all, of the tax payments attributable to the closely held business in up to 10 equal, annual installments, which don’t begin until five years after the estate tax is due. Only interest on the amount borrowed would be due during those first four years, with the first installment due no later than five years from the original estate tax payment due date.³

The Internal Revenue Service (IRS) will lend at a relatively low net interest rate provided the borrower meets stringent requirements; however, the annual interest payments are non-deductible. Other downsides to borrowing from the U.S. government include:

• The loan would be subject to a variable rate during its term⁴
• Bonds and/or tax liens are typically required
• Formal closing of the estate would be delayed

Government loans are available only to estates that have assets consisting of significant holdings in one or more closely held business interests and, even then, other limitations may also apply.⁵

Arrange for a Graegin loan

A so-called Graegin loan from a financial institution might satisfy a tax obligation.⁶

Often useful for estates that own closely held business interests, the loan also could be used separately – or in concert with government financing when applicable – to pay estate taxes attributable to other illiquid assets, or to pay state estate and inheritance taxes.

When properly structured, all of the interest due over the many years of the loan are immediately deductible for estate tax purposes (with no present value concept required in calculating the deduction).⁷

But note: In a Graegin loan, the interest due must be a fixed, exact amount when the loan is entered into, or by integrating a rate swap at inception with the same terms to fix a variable loan rate. This way, the interest is determinable immediately and, therefore, deductible currently. So while the term of a Graegin loan is negotiable up front, once the loan is finalized, it cannot be renegotiated or prepaid at a discount.⁸

This arrangement also may have other restrictions. For example, the creditor might require a minimum level of liquidity, limit distributions from the estate or prevent the imposition of any liens on estate assets.

Cash in corporate stock holdings

For estates that own closely held business interests in corporate stock, there is a special rule that permits redemption with typically no capital gains tax due – rather than as a taxable dividend when a corporation buys the stock from the estate.⁹

A big enough redemption should provide significant needed liquidity to an otherwise largely illiquid estate.

Alternate valuation might help

An “alternate valuation” might be able to reduce the estate taxes owed. U.S. tax law permits a new valuation of all property in an estate six months after the date of death. However, if property was distributed, sold or otherwise disposed of during that time, one would look to the date of disposition.¹⁰ This law is helpful to the beneficiaries if there’s been a decline in an estate’s entire value during those six months.

Another provision of the law relaxes, in certain circumstances, the fair market value standard normally required in valuing real property and related assets held primarily by estates of ranchers and farmers, instead permitting valuation of ranch or farmland based on its actual use.¹¹ Market conditions or other factors could make these attractive options.

We can help

Choosing an optimal tax payment strategy can be complex. Therefore, analyzing the options is best undertaken with the assistance of knowledgeable and experienced advisors.

Your J.P. Morgan advisor can work closely with you and your tax and legal advisors to compare potential solutions for obtaining liquidity for your estate.

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